The 4 weirdest dates Dean's ever been on
by Moppipoika
Summary: Dean gives the awkwardly flirting barista a chance. Sequel to "The 5 worst pick up lines Dean's ever heard"
1. Coffee

Even though Dean had no reason for it, he was nervous. He didn't really understand himself when it came to his anxiousness about the date he was having soon; he had been on the countless other dates before this, and he had never been nervous, so why now?

To Sam, it was if course funny to see Dean like that, and he had already spent the whole day laughing and snickering, telling Dean time after time that it was hilarious how he had a crush.

Dean didn't really feel that way; he didn't have a crush, Castiel had just seemed like a fun guy and now Dean decided to give the guy a chance since he had nothing else to do anyway.

They left the motel room together; Dean had a date and Sam had to go meet Rufus about something the man needed help with, and since Dean still had the damn cast on his hand he would've needed a ride anyway. This time, he was actually glad that Rufus had managed to fuck something up again, because he hated to ask Sam to drive him around, so now he hadn't had to because Sam had to leave either way.

"Have fun," Sam smirked as he pulled up to the side of the road so Dean could get off. "But not too fun, it's kinda slutty if you put out in the first date."

"Shut up, Sam," with an eye roll Dean got up from the car, motioned with his hands to his brother to keep going already.

When he was left alone, Dean took a moment to just breathe deep. He had nothing to worry about, he was a pro. He had been on so many dates he couldn't remember half of them; he'd survive this.

With slow, kind of shaky steps Dean entered the coffee shop, immediately spotting Castiel sitting next to the counter. The man's eyes once again lit up as he saw Dean approach him, and Dean had to admit he had already missed those eyes.

"Hello, Dean," Castiel smiled as he got up from his seat. "How are you?"

Dean bit his lower lip to keep himself from laughing over how weird it already felt. "Well, still pissed about the cast," he was soon able to answer.

"How long until you'll get rid of it?" Castiel asked, tilting his head a little. As he did so, he signed for one of his co workers to come to the counter. "Dean, this is Amanda," the man smiles as she approached. "She's gonna make us coffees, you know, to make up for the bad coffee I made you yesterday."

Dean let out a short laugh, and just when he was about to answer the man, Amanda decided to hold her hand out over the counter. Dean stared at it for a moment before he realized he was supposed to shake it. "Nice to meet you," he forced the words out with a pretentious smile.

"You too, Dean," Amanda smiled widely before letting go of his hand so that she could fix the drinks for the men.

Dean felt even weirder by the fact that Castiel had just introduced him to a co-worker. On their date. And the coworker had known Dean's name before Dean had even had a chance to introduce himself. To be honest, it even freaked him out a bit.

"How come I've never seen you and your brother here before?" Castiel casually leaned against the counter, his eyes fixed on Dean and a smile playing on his lips.

Dean had been so confused about Amanda, that the question got him off guard and it took him a moment to find the right words: "Uh, we move a lot," he shrugged, "you know, because of the job."

"Oh? I didn't know Hunter's' job was like that," Castiel's smile never faded, and it would've helped Dean to relax if he hadn't noticed how Castiel's co workers kept staring at them from a distance.

"Well, not always," Dean tried his best to focus on Castiel instead of the co workers, "But but we're more of a call us if you need something killed kind of hunters."

"So if there's like an emergency, you're the ones to take care of it."

"That's us," Dean nodded with a pleased smile. He had done this hundreds of times, but he was still kinda sure it had never been this easy to explain what he did for a living.

"Sounds interesting," Amanda's voice made Dean jump a little; he had definitely not expected for her to get involved in their discussion. "Even though you don't really look like a hunter to me," Dean wasn't sure if it was supposed to be a compliment or not, either way, he still felt like punching her at this point, "But how would I know, right? Anyway, here's your drinks."

Dean was more than happy to accept the drink, so he could just get the hell out of there with Castiel, but for some reason the man didn't really look like he was leaving.

"Castiel?" Dean furrowed as he turned back towards the man. "Are we going?"

"Where?" the man seemed confused. Dean had a bad hunch. "I thought we could stay here, you know, enjoy the coffees in a warm place instead of freezing outside."

Dean bit the insides of his cheeks, forcing himself to shut up about the fact that it was probably more chill in the café than outside. "Sounds, mh, nice," he forced a smile.

Castiel on the other hand seemed more than happy when they sat down at one of the few tables. To Dean, it was simply weird, but he decided to give the man a chance.

And he did not regret it. Castiel was funny, kind and easy to be with, even though the man's mind seemed to be filled with thoughts that felt a little weird to Dean. But he was definitely better company than the pick up lines had indicated for him to be.

What Dean didn't enjoy was the fact that Castiel's co workers seemed to have a lot of work to do near their table, and they didn't exactly try to hide the fact that they were eavesdropping on their conversation. If Dean told Castiel something funny while one of the workers were somewhere near, they laughed with Castiel. If Castiel told Dean he liked his hair, the nearest co worker smiled and nodded as an agreement on what Castiel had just said.

When Sam pulled up outside of the coffee shop, Dean felt a weight roll off of him and he practically jumped up from his seat.

"What? Already?" Disappointment flashed through Castiel's face as he realized Dean was going to leave.

"Oh, well, yeah," Dean rubbed his neck awkwardly, "He's my ride, and I really don't have the energy to-"

Castiel shook his head and hurried to interrupt Dean: "No, no! It's okay, Dean," the man gave him a warm smile. "I just hope we could've spent more time together."

With a melting heart, Dean suddenly heard himself promise the man a new date: "Maybe we'll meet again? With better time?"

"Sounds great," if possible, Castiel's smile got even wider.

"I'll call you when we get back to town," Dean promised before walking out of the building, straight to Impala where his brother was impatiently waiting for him.

"Well? Did it go well?" Sam's eyes were filled with curiosity and the need to know everything. "Are you gonna meet again?" His face dropped as

Dean gave him a simple shrug. "What? Was it that horrible?"

"It was a bit weird."

"But?"

"I'll give him a call if we're around."


	2. Opera

"So, it seems like we have to wait until tomorrow before we can actually do anything," Sam mumbled with a sigh as he closed his laptop's lid. "Anything you wanna do to kill some time?"

"Oh, I'm driving to see Castiel," Dean shrugged, "You can do yoga or go hiking or whatever hippie stuff it is you enjoy doing," he gave his brother a teasing smirk, "but I'm going on a date tonight."

"You're actually going to see him again?" Sam's eyebrows raised in surprise, "didn't you say the last date was the weirdest thing ever? Something about his co-workers-"

"- his co-workers practically hanging out with us, yeah," Dean finished his brother's sentence with a few short nods, the memory of the last date sending shivers down his spine, "But this time we're not gonna meet at the coffee shop."

"Where then?"

"I have no idea," Dean admitted with a shrug, "I let him plan it on his own."

It was a quarter past seven when Dean found himself standing in the middle of an empty market place, waiting for Castiel to appear from somewhere. He had a weird feeling about the place, and he was kind of afraid Castiel would never show up or that they'd spend the entire date there.

"Hello, Dean," a familiar voice came from behind, and Dean turned on his heels to see smiling Castiel approach him. "I'm sorry I'm late."

Dean had been a little mad at Castiel for making him wait like that, but the man's wide smile and bright eyes made all the annoyed thoughts fade away. "It's okay," he returned the smile, "I'm just happy you came."

"Of course I came," Castiel laughed, and Dean was pretty sure he saw a quick smirk on the man's lips.

"So," Dean rubbed his neck feeling a bit awkward, "what's the plan for tonight?"

"Opera," Castiel answered with a proud smile, and Dean could only raise his brows in surprise. He had went over countless amount of different things Castiel could've planned for them, but opera had definitely not crossed his mind. "You like opera, right?"

Again, Dean rubbed his neck awkwardly: "Well, I've never been to opera, but you know, it probably won't kill me trying it once."

"Oh," Castiel's face dropped, and Dean actually felt kinda bad for not lying. Sure it was kinda mean to lie about something like that, but then again, it would've been worth it to not see Castiel looking so heart broken.

"I'm sure I'll enjoy it," Dean hurried to give a small pat on Castiel's back, "besides, I don't care what we do, as long as it's just us. I mean, I just want to spend time with you and I don't care where."

"Thanks, Dean," Castiel's smile was small and a bit sad, but it was still a smile.

They walked in silence, both stealing glances at each other from time to time. There was a warm but a bit uncomfortable knot in Dean's stomach. He wasn't sure what it meant, but he was pretty sure it wasn't because of the bacon burger he had eaten earlier.

"So," Dean swung his hands back and forth in his sides when he had no idea what else to do with them since it for some reason felt somewhat rude to keep them in his pockets, "you go to opera often?"

"No," Castiel admitted with a smile, "I just thought it'd be, you know, fancy for a date."

Dean chuckled lowly: "And what exactly made you think I'm a fancy person?" Opera did sound like a, well, fancy option for a date just like Castiel had said, but he wasn't a fancy person. He was a man driving an Impala, hunting mythical creatures and gambling for a living.

"I guess I let my friends get a little too involved in planning the date. I really hope you don't hate the idea," Castiel laughed nervously, eyes glued to their feet as they walked, obviously too timid to look at Dean at the moment.

"No no, I don't hate it," Dean assured quickly. "I'm just not really into it, you know. I don't believe I'll love it, but I'm sure I won't hate it."

He tried to give the man an encouraging smile, but Castiel seemed to have lost all hope. "Castiel, listen," Dean sighed and stopped them both. "I don't care if it's a movie, opera or a bloody ballet we're going to," his voice was serious as he spoke. He carefully grabbed Castiel's chin to lift the man's face so he could see his eyes, then gave the man another smile.

"I came to spend time with you," he spoke quietly now, keeping the warm smile on his lips, "and I came to see you."

Castiel's cheeks were burning red by the time Dean was done, and he lowered his eyes again as soon as Dean let go of his chin. "That's great to hear," he slowly mumbled, "cause I think we're gonna be late from the show."

"What? Why?"

"I have no idea where the opera house is."

Dean tried his best to stay quiet, but he simply couldn't stop himself from laughing uncontrollably at the situation; Castiel wanted to take him to opera even though opera was the last thing on earth he had planned to go to, and now they were gonna be late because they had most likely gotten lost.

"Don't laugh, Dean," Castiel cried, but Dean could see the smile creeping on the man's lips. "This is serious! I thought it was here! I mean, I checked and asked from my friends and they said it would be here!"

Dean covered his mouth with his hand as he followed Castiel who was desperately trying to figure out where the opera house was located at. Not that Dean minded at all, he was more than happy to spend their time looking for the opera house rather than in the opera house.

After walking around the area for a good thirty minutes Castiel let out a defeated sigh. They hadn't spotted the opera house; not even a little sign pointing at the right direction had caught their eyes.

"Okay, alright, I give up," Castiel raised his hands.

"Good," Dean laughed and gave the man a pat on the back, "cause I'm starving."

"There's Pizza Hut nearby," Castiel gave him a sad smile. "Or there's supposed to be Pizza Hut nearby, but you never know when you're with me."

Dean gave Castiel a gentle nudge on the side: "Don't be so hard on yourself, I didn't really enjoy the idea of going to opera. Pizza Hut sounds way better."

Castiel smiled weakly. "Thanks, Dean."

As they were headed to the said fast food restaurant, Dean couldn't stop smiling. Castiel was telling a story about how he had almost managed to lose his job at Starbucks by tripping on his shoelaces and almost breaking a window, and for some reason just listening to the man talk forced the smile to stay on his lips.

It was like they had known each other for ages and Castiel was Dean's very best friend, except unlike when spending time with his friends, Dean had that uncomfortable, warm knot in his stomach when he was with Castiel. A warm knot that forced him to keep on smiling even though Castiel wasn't funny at all at the moment and he didn't feel like smiling.

At this point Dean had no problem admitting that giving Castiel another chance had not been a bad idea at all, it was actually as far from a bad idea as possible. He had gotten a little scared about the whole opera thing, but now that they had gotten lost and were eating pizza instead, Dean was happy. It was a little weird, but he didn't mind. A little weird was definitely better than opera.

"Castiel?"

Dean watched as the said man lowered the piece of pizza in his hand and raised his eyes to Dean. "What?" The man asked with his mouth full.

"I like this whole eating pizza instead of something fancy -thing," Dean smiled with a chuckle. "I'd like more of it."

"More?" Castiel almost choked in his pizza, staring at Dean with wide, surprised eyes. "You mean, like, another date?"

"Yeah, like another date."

"You sure?"

"I'm sure."

Castiel's surprised expression slowly turned into a relieved smile as Dean's words sunk in.

"What if we go to a movie next time?" Dean soon suggested with a smirk, managing to turn Castiel's cheeks red.

"Sounds great."


	3. Movies

"So," Dean took another fry from the tray they had between them on the table, "you wanna go see a movie?"

"Yes, that's correct," Castiel said with a nod and a victorious smile, "I want to go see a movie."

It was their third date, and everything had gone nice and smooth. They had met around 6 pm; Dean had picked Castiel up from work and they had driven around for a good hour, just talking and listening to some music. Castiel had seemed to like the music Dean listened, and it had rolled a huge weight off his shoulders; he could never date anyone who didn't like his music.

After that, they had picked up a place to eat; a small place that served all kind of burgers and pizzas. Dean had gotten himself a massive double-bacon-monster-burger with extra fries, and Castiel had picked a small cheeseburger. The food had been awesome, and even though Dean liked to think his stomach was an endless pit, he had to admit he was actually pretty stuffed.

That was why they had moved his fries to the center of the table and they were both nibbling them as they spoke. It was easy and chill. Castiel had seemed to enjoy himself the whole evening, and Dean definitely had; it was just the kind of date he liked. Even thinking about Castiel's idea of going to the opera for their last date made him shiver.

"Which movie?" Dean asked after taking a sip of his cola.

"Happy Feet," Castiel answered with a wide smile, "I want to go see Happy Feet."

"Happy what?" Dean raised his brows, feeling a bit confused. He didn't really go to the movies that often since he rarely had any nights off, so he didn't always know the names of the new films, but he definitely hadn't heard about that one.

"Happy Feet," Castiel repeated with a chuckle, "It's a kids' movie." Dean fought the urge to roll his eyes. "It's a story about a penguin who can't walk properly, but he can dance and everyone thinks he's a freak because of it, and-"

"Yeah, yeah," Dean cut him off, nodding his head, "I get the picture. Don't spoil it too much for me."

At that, Castiel's eyes brightened. "Are we going to see it?" he asked, his voice full of hope and happiness. His whole presence was glowing with excitement, and Dean couldn't help but smile.

"Yeah," he said with a nod, "we're going to see it."

* * *

The whole movie made Dean want to either roll his eyes for a straight hour and a half or to run away from the movie theatre, crying his eyes out from both laughter and sadness. It was terrible and fantastic at the same time, and Dean was surprised by the movie in every single way. He was surprised he actually enjoyed it and he didn't fall asleep. He was also surprised it almost made him tear up, it also made him laugh; a lot. They had both laughed so much their stomachs' were hurting and their eyes were reddish and a bit puffy from the tears of joy.

When they left the theater, Dean was left alone for a moment as Castiel excused himself to powder his nose, which had made Dean chuckle to himself; nobody said that. Nobody but Castiel. And that made Castiel so, very awesome. Dean really liked hanging out with him; he felt easy and relaxed like he didn't have to try at all, it all came naturally. They had only been on three dates, and it sounded cheesy as hell, but he had actually never thought he could feel like that with somebody else than his brother.

"So how was tonight?" Dean asked as they were driving through the town.

"It was great." Castiel flashed him the widest, brightest smile he had ever seen, and he was convinced. A man couldn't lie and smile like that, it just wasn't possible.

"I think so too," Dean admitted with a smile. He really did. It had been amazing even. "I mean I was skeptical about the movie-"

"What was wrong with the movie?" Castiel cut him off with his question, his eyebrows in a concerned furrow

"Nothing!" Dean hurried to say. "Nothing! It's just.." he cut himself off with a sigh. "I mean, I didn't really expect anything great from a kids' movie, that's all. But it turned out great!"

Castiel eyed him for a moment until he finally seemed to decide he accepted his answer and smiled again. "I know!" he said his voice dripping with excitement. "I was gonna go see it a few days ago already, but then you called and I decided I wanted to go see it with you instead."

Dean's heart melt. Castiel was a sweet guy, a little too sweet even. He had been so excited to see the movie, but still, he had waited to see it with Dean, even though he hadn't even known if Dean wanted to see it or not. There had been a huge chance he would've said no. But he was glad he hadn't.

Of course, it had been a bit weird, but after two extremely odd dates, it was kind of what Dean had expected for anyway. And it wouldn't have been the same if they had been on a normal date, Castiel wasn't normal. He was weird and funny and kind.

"Thanks," Castiel smiled as Dean walked up to him. They had pulled up on Castiel's driveway just a few seconds ago. "This was really a great evening."

"Yeah," Dean let out a somewhat awkward laugh and rubbed his neck, staring at his shoes for a moment, "it was."

"So we'll see again?" Castiel asked with a raised brow and a shy smile, and Dean didn't know what had gotten into him, but he felt how his cheeks started to burn.

"We'll see again." He managed to nod before Castiel wrapped his arms around him, hugging him tightly. After a short moment of being kind of shocked, he shook himself out of it and returned the hug. It was a tight, warm, and loving one; the kind that made Dean's tummy all warm and his heart beat a little faster.

"I'll wait for your call," Castiel whispered before pulling away.

Dean couldn't open his mouth anymore. He just stared at Castiel disappear through the front door, wondering what the warm feeling inside of him was. He couldn't come up with an answer until he had driven away and was waiting in red lights, staring into the horizon; he was falling for Castiel. He was falling hard.


	4. Paintball

"So?" Sam asked after taking a bite from his veggie burger.

Dean threw away the empty wrappers of the burger he had eaten and raised his brow in a questioning manner. "What?" he asked even though he knew damn well what Sam wanted to know.

"Where are you going today?" Sam asked.

"Apparently he's taking me paintballing," Dean told his brother with a chuckle. "Don't ask me why, because I have no idea, but it sounds better than opera so I agreed."

"Paintballing, huh? Sounds romantic," Sam commented with a bored voice as he eyed through the morning paper. They hadn't found a case for them to investigate, which was why Dean had decided to call Castiel so they could go out on another date, and Sam was desperately trying to find them a new case because they were both bored out of their minds.

"Yeah, I know, I totally wished he would take me to see a ballet," Dean joked and received an amused eye-roll from Sam. "Seriously Sam, you think I really care about romance? Besides, what could be more romantic than paintballing?"

"I don't know, probably anything," Sam laughed and shook his head.

"Well we don't need your opinion on that," Dean told his brother before pouring the rest of his drink down his throat.

* * *

At three, Dean pulled up at Castiel's driveway and smiled widely at the black haired man that got in his car. It had been almost two months after their last date, but it had felt like years. Of course they had been texting pretty much every day and even spoken on the phone a few times, but it was so different from actually seeing each other in person. For example, when they spoke on the phone, Dean wasn't nervous at all. But now that Castiel was once again sitting next to him, an uncomfortable know appeared in his stomach and he felt like everything he said sounded extremely stupid.

But apparently, Castiel didn't think Dean sounded stupid at all. Through the whole drive they talked about work, food, tv-shows they liked, and everything between, and Castiel never stopped laughing at Dean's jokes. He even laughed at the ones that made Dean cringe at himself. But the fact that even those kind of jokes managed to make Castiel laugh made Dean even happier that it was Castiel he was on a date with.

Dean parked the car in the middle of a huge, gritty parking lot. He turned to Castiel, who was already about to get up from the car, but stopped when he realized Dean was staring at him.

"What?" Castiel asked, a hint of worry in his voice. "Something wrong?"

"No! Everything's fine," Dean hurried to answer with a smile. "Just wondering, why paintballing?"

A faint blush appeared on Castiel's cheeks, and Dean felt like his heart had done a backflip. "I, uh… I just thought, you know, you work with guns and all that stuff so you must be pretty into shooting stuff, and I wanted to do something you'll actually enjoy. So, since the idea of touching a real gun frightens me, I thought paintballing would be something we'll both enjoy."

Dean couldn't stop smiling. Castiel was absolutely adorable. "Well you're right," he admitted with a shrug, "I am pretty excited about this."

They got up from the car and made their way inside where other people were already waiting, their hands slightly brushing against each other the whole way there. They were given all the equipment they needed, and after they had changed into the camouflage suits, they were informed that they would have to go on different teams or the teams wouldn't be equal. And since nobody agreed to change teams, they simply decided to roll with it.

"Sorry we can't be on the same side," Castiel mumbled as they waited to get into the playing area.

"It's not your fault," Dean said with a smile. "Maybe you'll get in my team on the next round." The doors opened, and Dean gave Castiel one last hug. "Good luck, Cas. You're gonna need it." With a teasing smirk on his lips, Dean winked at Castiel before running off to the other side of the hall.

And Dean had been right. With Dean on the team, they were overpowering, and there wasn't really anything the other team could do but to just hope Dean wasn't the one they were gonna run into while trying to reach the other team's base. It was a simple game of capture the flag, and it was supposed to be a game people played when they wanted to switch their brain off for a moment and just run around with a paintball gun, shooting at strangers. But Dean took it way too seriously because that's the way he was with a gun in his hands. The only person he refused to shoot at, was Castiel, but that was only because it felt weird to even think about shooting at his date.

But then came the last round, it had somehow gotten to a tie, and one of the opposite team's members had gotten extremely close to Dean's team's flag. They had decided to let Dean handle it, so he was slowly approaching the flag, trying to locate his enemy, ready to pull the trigger as soon as he'd get his eyes on the bastard. Suddenly someone ran from behind the corner, reaching for the flag. And just as their fingers were wrapping around the flag, Dean shot. And right after he had pulled the trigger, he realized it was Castiel.

* * *

"What the hell happened, Dean?" Sam was trying to keep his voice down as he walked up to Dean, who was sitting in the waiting lobby of the local hospital.

"Nothing! We were just playing paintball," Dean quickly defended himself and threw his hands in the air. "And I might have accidentally shot him in the head while playing.

"You what?!"

"Alright, hold your horses, Sam." Dean smiled awkwardly at an old lady who was staring at them like they had just broken the law by talking too loud. Dean didn't really understand, because it was a hospital, not a library, but he decided to just let it go. "It's not that serious, I mean yeah he did black out after that and we had to call him an ambulance, but he's fine now."

"How did you even- "

"I have no idea," Dean cut his brother off with a simple shrug.

Sam let out a sigh and sat on the chair next to Dean. After a short while they turned to look at each other, both of them unable to hold the laughter in anymore; simultaneously they started laughing at the situation.

"Maybe opera would've been a better option this time," Sam chuckled, wiping tears from the corners of his eyes.

"Yeah," Dean agreed, "probably."

After the brothers had managed to calm down a bit, a nurse walked out of one of the rooms nearby and walked up to them.

"Which one of you is Dean?" she asked with a polite smile, and Dean got up from his chair. "Castiel asked for you."

Dean followed her into the room Castiel was in, and after they had been left alone he sat down on the chair that was located beside the bed. For a moment he stared at the floor with an embarrassed blush on his cheeks before he dared to raise his eyes to Castiel.

"You okay?" he carefully asked.

Castiel chuckled. "I'm fine, they just wanted to take some tests. You know, just to be sure," he explained with a smile. "It was probably because it was the first time they had heard someone passed out because they had been shot with a paintball gun."

An amused smirk made its way to Dean's lips. He had to admit it sounded a bit unreal, and way funnier than it probably should.

"I didn't mean to shoot you," he said soon, even though he was sure Castiel knew that. "I'm so sorry our date ended like this."

"It's okay Dean," Castiel assured him with a short laugh. "I had fun."

"You did?"

"Yeah."

"You know what," Dean smiled, "so did I. I never know what to expect with you, and that's why I like you."

Castiel's lips curved into a smile so wide it almost reached from ear to ear. "I like you too, Dean," he said, his cheeks slowly turning red.

Dean was a hundred percent sure that every cell in his body backflipped from happiness, and his legs felt like they were gonna give up when he got up from his chair. Slowly he leaned closer to Castiel and pressed a gentle kiss on the man's forehead.

"C'mon," Dean said quietly, his smile never fading from his lips, "let's go grab something to eat."

 **/ AUTHORS NOTES - Here we are! Thank you all for reading, commenting and favoriting this fic! It means so much to me! I'm gonna shamelessly advertise myself a little before you leave, because! There's more to this story! There's THREE sequels left, and the next one will be heaven for all the fluff lovers ;)**


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